Tetramic acid antibiotics: Stereoselective synthesis of streptolic acid and tirandalydigin

Angewandte Chemie - International Edition

Volumn 44, Issue 10, 2005, Pages 1532-1536

  Iwata, Yasuhiro ^a   Maekawara, Naomi ^a   Tanino, Keiji ^a   Miyashita, Masaaki ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

Antibiotics; Asymmetric synthesis; Methylation; Natural products; Stereoselectivity

Indexed keywords

ANTIBIOTICS; SYNTHESIS (CHEMICAL);

STEREOSELECTIVE SYNTHESIS; STREPTOLIC ACIDS; TETRAMIC ACIDS; TIRANDALYDIGIN;

ORGANIC ACIDS;

ANTIBIOTIC AGENT; DICHLOROMETHANE; DNA DIRECTED RNA POLYMERASE; STREPTOLIC ACID; STREPTOLYDIGIN; TETRAHYDROFURAN; TETRAMIC ACID DERIVATIVE; TIRANDALYDIGIN; UNCLASSIFIED DRUG;

ACETALIZATION; ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; EPOXIDATION; HYDROLYSIS; STEREOCHEMISTRY;

AMINOGLYCOSIDES; PYRROLIDINONES; STEREOISOMERISM;

EID: 16244401160     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200462300     Document Type: Article

References (30)

1. a) K. L. Rinehart, Jr., D. B. Borders, J. Am. Chem. Soc. 1963, 85, 4037;
2. b) F. Reusser, Antimicrob. Agents Chemother. 1976, 10, 618;
3. c) J. P. Karwowski, M. Jackson, R. J. Theriault, G. J. Barlow, L. Coen, D. M. Hensey, P. E. Humphrey, J. Antibiot, 1992, 45, 1125.
4. a) R. E. Ireland, P. G. M. Wutz, B. Ernst, J. Am. Chem. Soc. 1981, 103, 3205;
5. b) R. H. Schlessinger, G. R. Bebernitz, P. Lin, J. Am. Chem. Soc. 1985, 107, 1777;
6. c) P. DeShong, S. Ramesh, V. Elango, J. J. Perez, J. Am. Chem. Soc. 1985, 107, 5219;
7. d) R. K. Boeckman, Jr., J. E. Starrett, Jr., D. G. Nickell, P. E. Sum, J. Am. Chem. Soc. 1986, 108, 5549;
8. e) C. Neukom, D. P. Richardson, J. H. Myerson, P. A. Bartlett, J. Am. Chem. Soc. 1986, 108, 5559;
9. f) R. E. Ireland, M. G. Smith, J. Am. Chem. Soc. 1988, 110, 854;
10. g) S. F. Martin, C. Gluchowski, C. L. Campbell, R. C. Chapman, Tetrahedron 1988, 44, 3171;
11. h) S. Ikegami, T. Katsuki, M. Yamaguchi, Tetrahedron Lett. 1988, 29, 5285;
12. i) I. Paterson, M. A. Lister, G. R. Ryan, Tetrahedron Lett. 1991, 32, 1749.
13. a) C. E. Meyer, J. Antibiot. 1971, 24, 558;
14. b) H. Hagenmaier, K. H. Jaschke, L. Santo, M. Scheer, H. Zaehner, Arch. Microbiol. 1976, 109, 65.
15. a) T. E. Elbe, C. M. Large, W. H. DeVries, G. F. Crum, J. W. Shell, Antibiotics Annual 1955-56, Medical Encyclopedia, New York, 1956, p. 893;
16. b) K. L. Rinehart, Jr., J. R. Beck, D. B. Borders, T. H. Kinstle, D. Krauss, J. Am. Chem. Soc. 1963, 85, 4038;
17. c) D. J. Duchamp, A. R. Branfman, A. C. Button, K. L. Rinehart, Jr., J. Am. Chem. Soc. 1973, 95, 4077.
18. G. M. Brill, J. B. McAlpine, D. J. Whittern, J. Antibiot. 1988, 41, 36.
19. a) M. Miyashita, M. Hoshino, A. Yoshikoshi, J. Org. Chem. 1991, 56, 6483;
20. b) M. Miyashita, T. Shiratani, K. Kawamine, S. Hatakeyama, H. Irie, Chem. Commun. 1996, 1027;
21. c) N. Ishibashi, M. Miyazawa, M. Miyashita, Tetrahedron Lett. 1998, 39, 3775;
22. d) K. Komatsu, K. Tanino, M. Miyashita, Angew. Chem. 2004, 43, 4441; Angew. Chem. Int. Ed. 2004, 43, 4341.
23. d) K. Komatsu, K. Tanino, M. Miyashita, Angew. Chem. 2004, 43, 4441; Angew. Chem. Int. Ed. 2004, 43, 4341.
24. K. Maruyama, M. Ueda, S, Sasaki, Y. Iwata, M. Miyazawa, M. Miyashita, Tetrahedron Lett. 1998, 39, 4517.
25. a) D. A. Evans, L. K. Truesdale, Tetrahedron Lett. 1973, 49, 4929;
26. b) D. A. Evans, L. K. Truesdale, G. L. Carrol, J. Chem. Soc. Chem. Commun. 1973, 55.
27. Y. Ito, S. Fujii, T. Saegusa, J. Org. Chem. 1976, 41, 2073.
28. K. Thomas, K. Reinhard, A. Bruno, S. Fritz, Chem. Ber. 1982, 115, 1810.
29. S. V. Ley, S. C. Smith, P. R. Woodward, Tetrahedron 1992, 48, 1145.
30. Although removal of the N-2,4-dimethoxybenzyl group in 31, leading to tirandalydigin (2), was examined under various conditions, this transformation has not been successful so far because of the susceptibility of the vinyl epoxide moiety to acidic conditions. We will discuss the removal of the protective group in detail in a full paper.